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Benzyl Chloride, C0H5CH2C1

Cannizzaro, Annalen, 1853, 88, 129.

100 grms. toluene.

i           phosphorous trichloride.

The apparatus consists of vessels for evolving and drying chlo-
rine (see Fig. 62, p. 88) and a weighed retort (300 c.c.) standing"
on wire-gauze, into which the toluene is brought. (Fig. 80.)
chlorine enters through an inlet tube, fixed through the t
of the retort, the neck being fixed to a reflux condenser.

FIG. 80.

dry chlorine is conducted into the toluene, which is kept boiling:
gently until it has gained about 37 grams in weight.* The liquid.
turns yellow, and hydrochloric acid fumes are evolved sit tlie
upper end of the condenser. When the reaction is complete tlie
contents of the retort are distilled.* At first unchanged toluene
distils ; the fraction boiling at 165185 contains nearly *tlie
whole of the benzyl chloride, and forms the greater pa,rt of
the product. The liquid, which passes over above 185, is a
mixture of higher chlorinated compounds, and consists cl~k.iefly
of benzal chloride, C6H5CHC12, and benzotrichloride, C6F